


Lola

by drdean



Category: Supernatural
Genre: Anal Fingering, Anal Sex, Blow Jobs, Bottom Castiel, Dean Doesn't Know, Dean is In Over His Head, Dean's First Time, Dean's First Time With a Man, Feminine Castiel, Feminization, First Time, First Time Blow Jobs, First Time Topping, First Time for Everything Fest, Hand Jobs, I Blame Tumblr, Inspired by Music, M/M, Making Out, Mistaken Identity, Smut, Tags Contain Spoilers, Top Dean, cross dressing
Language: English
Status: Completed
Published: 2016-08-25
Updated: 2016-08-25
Packaged: 2018-08-10 21:30:30
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,279
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7861795
Author URL: https://archiveofourown.org/users/drdean/pseuds/drdean
Summary: <blockquote class="userstuff">
              <p>Based of the song Lola by The Kinks</p>
<p>Dean meets Cas at a bar, if you know the song you know what happens.</p>
            </blockquote>





	Lola

**Author's Note:**

> Lola has been stuck in my head, so this had to be done.
> 
> Thanks to [mindylee](https://archiveofourown.org/users/mindylee/pseuds/mindylee) for betaing.

Dean had never left Kansas before. And he had just moved to the big city the week prior and was still trying to figure everything out. He was grabbing a beer down in SoHo, and he swore that it tasted more like coca cola then whatever it was that he ordered, maybe they had their taps crossed? It was dark in the bar and they were playing loud music. Well, with all the people dancing he guessed that it could be considered more of a club then a bar. But he had never been to a club before, so he wasn’t sure. He was leaning back against the bar and looking around checking out everyone when his eyes locked with the most beautiful blue eyes that he had ever seen. The owner of said blue eyes winked at him and sauntered over.

“Hey” Dean was a little surprised at how her voice sounded. “Do you want to dance?”

“What’s your name?”

“Cas” Her voice was deep and seemed to drip with sex. It was much deeper than most women’s voices, maybe she was a smoker? But she didn’t smell like a smoker.

“Dean” He held out his hand and she took it and lead him out onto the dance floor.

Dean put his hands on Cas’s hips as she swayed with the music. Cas could really move her hips. She was tall for a woman, only a few inches shorter than Dean. She had long black hair, it was all messy from dancing most likely, but it kinda looked like sex hair too. Dean wanted to run his hand thru it and mess it up even more. She was wearing a tight dress that really hugged her boobs and her ass. She had great legs and the dress was short enough to showed them off. Dean thought that she must run or workout to have legs like that.

They danced together for a while before a slow song came on. Cas gripped Dean tight and Dean was amazed at how strong she was, no woman had ever held him so tightly before. Dean gripped her back tighter too and it quickly turned into an unspoken contest between the two to see who could hold on tighter to the other one. Cas won. Dean smiled at her, and she smiled back.

When they went back to the bar for a drink, Cas sat down on a bar stool and picked Dean up and put him on her lap. She wrapped an arm around his waist. “Little boy won't you come home with me?” Her eyes shone up to him with hope.

Dean had never seen eyes like that, and he almost fell for her right then. There was no way that he wouldn’t follow her wherever she wanted to go. Dean wrapped his arms around her, which was slightly awkward for him, he never thought that he would be the one sitting on a woman’s lap, but Cas was surprising him all night with her strength that was seemingly in opposition of her great looks and the sexy, sultry way that she moved. He smiled at her and said, “Of course sweetheart. Lead the way.”

Cas beamed up at him, and almost jumped off the seat. She seemed giddy with excitement, as she led Dean out onto the street. She pushed him up against a wall to kiss him hungrily not even a block away. At first Dean was so shocked that he didn’t even kiss back. But by the time he felt Cas’s tongue at his lips, he gladly opened up to accept and switched their positions so that Cas was the one up against the wall. “Little boy, we need to move or I will just have to have you right here.” Her already low voice seemly got even deeper. She took Dean’s hand and lead him away towards her apartment.

“Yeah, yeah that's a good idea.” Dean responded when his fog lifted slightly. “I’ve never done that before.”

“Had sex on the street?” Cas turned her head back to wink at him as they walked.

“No, I mean, ya, that too. But I’ve never made out with someone.”

Cas stopped and immediately spun around to look at Dean. “Really? How has someone as hot as you never made out with someone?” She looked shocked.

Dean felt himself go red and he pulled his hand away from her so he could rub the back of his neck. He couldn’t look Cas in the eye, so he looked at her shoes. They seemed kind of big for a woman, but the thought didn’t fully register in his brain. “Ya, well, um, I come from a really conservative small town in Kansas. The girls there didn’t want to do anything with a guy before they had a ring. And I just moved here a week ago. So, um, ya.”

“Oh, don’t you worry about anything. Little boy, I’m gonna make you a man.” Dean looked up and Cas winked at him before giving him a quick peck on the lips, grabbing his hand again and almost sprinting the rest of the way to her apartment.

Her place was a small walk up studio. It didn’t have a lot of feminine touches but that was just fine with Dean. It was clean and it had a bed. Dean gave her a little push towards the bed, and she sat down on the edge. Dean fell to his knees and looked up at her. “Please,” he wanted her so much, more than he had ever wanted anyone, “Show me what to do.”

She pulled Dean up to sit beside her at the foot of the bed, and kissed him, with just as much passion as before. “Don’t worry little boy, I will take care of you.” Her hands slid to the front of his shirt and she began unbuttoning it before taking it off. She then reached for the hem of his t-shirt and pulled it off, only to break the kiss to get it over his head. “Mmm little boy, you are quite the fine specimen of man.” She said as she ran her fingers over his chest. She continued divesting him of his clothes until he sat on her bed completely naked. She stroked his hard cock slowly, and Dean thought that he would come right then. No one else had ever touched him before, and it felt so much better than when he touched himself. Dean closed his eyes, tilted his head back and moaned.

“This isn’t fair.” Dean said as he tried to gain some control over himself so that he wouldn’t come embarrassingly quick. “You should be naked too.” Dean brought his arms around her back to unzip her dress. Cas started aggressively kissing him, so that most of his attention was on making out with her and he couldn’t see what he was doing and had to do it all by feel. He was able to unzip the dress just fine, but he struggled for a minute trying to unhook her bra. Who knew how hard those things could be! Once he got that undone, he moved to take them both from her broad shoulders. She helped move her arms out of the dress and the bra, but continued to kiss Dean, almost as if her life depended on it. Dean moved the dress down her body and she lifted up her hips to let him take it off completely. Dean felt her satin paties and grabbed those too, to get her completely naked. After her clothes were off he pulled her in close and felt something between them. He went to move it out of the way when he touched it and Cas moaned. Dean couldn’t see, but he gave it a few experimental tugs and froze. _Cas is a man!_

Dean pulled back from the kiss and stared down. Cas’ dick was still in his hands. “Y-you’re a g-guy!” Dean stuttered out in surprise. Suddenly a lot of the little details that Dean had dismissed as odd, made sense.

“Yes little boy, I thought that was pretty obvious.” Cas stroked Dean’s still hard cock causing Dean to grip harder on Cas’

“I-It wasn’t too m-me. At least u-until j-just now.”

Cas raised his eyebrows, “Oh little boy, you really do have so much to learn.”

Dean wasn’t sure what to do. He wasn’t gay. He had never been into men before. But he wanted Cas. She _-he-_ was so soft, yet hard, she _-he-_ was still beautiful and feminine, with makeup, long hair and no body hair. His dick was obviously still in the game as he felt it get even harder (wait was that even possible, he was painfully hard before) as Cas slowly stroked him while he kissed Dean’s neck. Dean knew he had to come, it would be too painful not too. His mind was already foggy with alcohol, lust and desire. He had never felt this good before, so he decided to just let go and freak out about it later. Dean moaned as Cas sucked harder on his neck and gripped onto his cock tighter. “S-shit”

“Does it feel good little boy?”

Dean moaned “Oooh yessss.”

Cas laughed “Don’t come yet little boy I still have so much to show you. And I promised to make you a man.”

“W-what does making me a m-man m-mean?” Dean had ideas, but he had to know for sure.

“You’re going to fuck me Dean, you’re going to lose that v-card of your’s tonight.”

Dean’s eyes went wide “C-cas!! You n-need to s-stop then!”

Cas looked smug “Oh? You don’t want to blow your load too early then?” Cas’s hand clamped down hard at the base of his dick to act like a cock ring, it did seem to help. “Well I guess you can watch as I open myself up for you then.” Cas let go of Dean and he whined at the loss of his touch. “You are a needy one aren’t you little boy? Don’t worry, I’ll take care of everything. Go lay down.” Cas pushed him towards the top of the bed and crawled over him to be able to reach into the nightstand drawer. He pulled out a bottle of lube and slicked up his fingers. He straddled Dean as he pushed two fingers in.

Dean didn’t really have a great view of what he was doing with his hands, but he could hear the squish and see the pleasure on Cas’s face. He took a few deep breaths to try and calm down. He never thought that he would find a guy so hot, but the sight of Cas opening himself up while on top of Dean was way hotter than any porn he had ever watched.

Cas took some more lube onto his fingers and pushed it into himself. He move down the bed a bit so that he could lower his mouth onto Dean “I think it’s time to get you all slicked up little boy.” Dean didn’t even have time to think what that meant before Cas’ lips and wet tongue were wrapped around his dick. Dean cried out with the pleasure of it. It was so warm, and wet. He had never felt anything like it. Cas continued to give him an extra sloppy blow job, taking every opportunity to spit on him to get his dick all slick. When Cas was satisfied that Dean had enough saliva on his dick, he pulled his mouth away, and then sank down on top of him so that Dean was inside him.

Dean grabbed onto Cas’ hips and bucked up into him. Again he was overwhelmed with the new feeling. It was warm and wet like the blow job, but it was also tight, and softer, and it was just so much more. “F-fuck!”

Cas smirked as he rolled his hips slowly. “You like that little boy? You like what it feels like to be a man?”

“Y-y-yes!” Dean was trying hard not to make Cas speed up, he wanted to so badly, but he was afraid to go any faster as he was already dangerously close to the edge.

“Mmmmm little boy, you don’t feel so little inside of me.” Cas started to slowly jerk himself off with his hand that was already slick from lube. “You feel like a man to me.” Cas leaned down and kissed Dean, and Dean hungerly tried to deepen the kiss and griped on to his hips even harder. “You like that don’t you little boy? Are you going to come inside of me like a good little boy?”

“Y-yes! Anything for you!” And Dean truly meant it. Cas had already given him more pleasure than anyone else had and Dean would do anything to repay the favor, and hopefully get even more in return.

Cas picked up the pace with his hand and with riding Dean. He had them both moaning with delight. Dean came first and Cas followed soon after painting Dean’s chest with cum. Cas reached over to the nightstand, this time for some wet wipes. He cleaned off Dean carefully, before sliding off of him and cleaning up himself. Dean already seemed to be blissed out and half asleep.

“It's okay little boy, go to sleep. Stay the night. We can do it again in the morning.” Dean smiled as Cas wrapped himself around Dean.

_Well that was totally unexpected, but awesome._ Dean thought right before passing out for the night. He could freak out in the morning. If he felt like it.

**Author's Note:**

> Lola by The Kinks:
> 
> I met her in a club down in North Soho  
> Where you drink champagne and it tastes just like cherry cola  
> C-O-L-A cola.
> 
> She walked up to me and she asked me to dance.  
> I asked her name and in a dark brown voice she said, "Lola"  
> L-O-L-A Lola, lo lo lo lo Lola
> 
> Well, I'm not the world's most physical guy,  
> But when she squeezed me tight she nearly broke my spine  
> Oh my Lola, lo lo lo lo Lola
> 
> Well, I'm not dumb but I can't understand  
> Why she walk like a woman and talk like a man  
> Oh my Lola, lo lo lo lo Lola, lo lo lo lo Lola
> 
> Well, we drank champagne and danced all night,  
> Under electric candlelight,  
> She picked me up and sat me on her knee,  
> And said, "Little boy won't you come home with me?"
> 
> Well, I'm not the world's most passionate guy,  
> But when I looked in her eyes,  
> Well I almost fell for my Lola,  
> Lo lo lo lo Lola, lo lo lo lo Lola  
> Lola lo lo lo lo Lola lo lo lo lo Lola
> 
> I pushed her away. I walked to the door.  
> I fell to the floor. I got down on my knees.  
> I looked at her, and she at me.
> 
> Well that's the way that I want it to stay.  
> And I always want it to be that way for my Lola.  
> Lo lo lo lo Lola.
> 
> Girls will be boys, and boys will be girls.  
> It's a mixed up, muddled up, shook up world,  
> Except for Lola. Lo lo lo lo Lola.
> 
> Well I left home just a week before,  
> And I've never ever kissed a woman before,  
> But Lola smiled and took me by the hand,  
> And said, "Little boy, gonna make you a man."
> 
> Well I'm not the world's most masculine man,  
> But I know what I am and I'm glad I'm a man,  
> And so is Lola.  
> Lo lo lo lo Lola. Lo lo lo lo Lola.  
> Lola lo lo lo lo Lola. Lola lo lo lo lo Lola


End file.
